Molecules comprising one or more β-hydroxyamine moieties, include, but are not limited to, poly(β-hydroxyamino)silicones, poly(glycidylamino)silicones, poly(β-hydroxyvinylamines) and poly(β-hydroxyethylenimines). Such polymers are used in premium consumer products for benefits such as softness, hand, anti-wrinkle, hair conditioning/frizz control, color protection, etc. Unfortunately, molecules comprising a β-hydroxyamine moiety, including current aminosilicones, are expensive, difficult to produce requiring long reaction time, large reactors and high temperature during the reaction process. Current technologies for producing molecules comprising one or more β-hydroxyamine moieties are typically expensive and/or difficult to process due processing conditions and limited processing efficiencies. Thus, what is needed is an economical, safe technology for producing molecules comprising one or more beta-hydroxyamine moieties.
Applicants previously disclosed the use of certain protic solvents in the production of aminosilicones. Unfortunately, the process of making such β-hydroxyaminosilicones was not as efficient and therefore not as economical as desired. Applicants recognized that the source of the inefficiency and cost was that the current protic solvents did not have a sufficient number of the correct type of hydroxyl groups in the required proximity of the groups to each other. In short, Applicants recognized that as the hydroxy equivalent/gram of a protic solvent increases, the catalytic activity of the protic solvent increases, that primary and/or secondary hydroxyl moieties provide better catalytic activity than tertiary hydroxyl moieties, that as the proximity of such hydroxyl groups in the protic solvent molecule increases, the catalytic activity of the protic solvent increases and that as the solubility of the protic solvents in the amine feedstock decreases the catalytic activity of the protic solvent decreases. Thus, if a protic solvent is judiciously selected such that it has sufficient solubility in the amine feedstock, contains at least two hydroxyl moieties, preferably at least one of the moieties being a primary and/or secondary hydroxyl moiety, contains the maximum number of hydroxy equivalents/g and such hydroxyl equivalents are in the maximum proximity, for example alpha-beta proximity, alpha-gamma proximity or alpha-delta proximity, the process efficiency can be dramatically improved. A further benefit of such discovery is that flash point of such judiciously selected protic solvents is typically higher. Thus, the safety of the process is improved. This increase in safety decreases costs, as explosion proof processing equipment and transportation equipment/procedures may not be not required. Applicants recognized that the aforementioned benefits not only applied to the production of aminosilicones but to any molecule that comprises one or more one or more beta-hydroxyamine moieties.
Thus, Applicants disclose certain highly effective, economical processes for producing molecules that comprise one or more one or more beta-hydroxyamine moieties, for example aminosilicones, as well as the use of such molecules.